I assume you know that Old Commonwealth is a now-defunct bottling that Julian Van Winkle assures us contained the same bourbon as the ORVW 10/107 of that period. I still have one bottle squirreled away.

Neither of the gentlemen on the label bear any resemblance to any photos I've seen of any of the Van Winkles. I'd guess they were intended to resemble what the general public thinks Kentucky gentlemen, perhaps a father and son, judging from the contrasting colors of their hair, should look like.